


Till I Kissed You

by Victoria_Grantt



Category: Supernatural
Genre: 1940s, 1950s, Alternate Universe, Alternate Universe - 1950s, Alternate Universe - Historical, Alternate Universe - Road Trip, Bottom Dean, Castiel and Dean Winchester Grow Up Together, Dinosaurs, Elementary School, First Kiss, First Time, First argument, Friends to Lovers, Friendship, Frottage, Growing Up, Growing Up Together, Hand Jobs, M/M, Orgasm Delay/Denial, Road Trips, Romance, Shower Sex, Slow Build, Vignette
Language: English
Status: Completed
Published: 2016-03-05
Updated: 2016-03-18
Packaged: 2018-05-24 23:11:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 15
Words: 19,121
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6170416
Author URL: https://archiveofourown.org/users/Victoria_Grantt/pseuds/Victoria_Grantt
Summary: <blockquote class="userstuff">
              <p>Dean and Castiel meet on the first day of school and quickly became best friends.  In the summer before they begin college, they take a road trip to Florida. Away from family and the eyes of their small town, they come to the realization they’ve been falling in love for years.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> For those that might be interested in such things, this is a partial list of the music Dean and Cas were singing and/or listening to as they grew up and on their road trip. I didn’t include every song I listened to while writing this. Let’s just say coming back from ‘50’s music to the 21st century, I experienced culture shock every time. 
> 
> Music
> 
> RoseMary/Fats Domino
> 
> Sh-Boom/The Crew-Cuts 
> 
> Book of Love/The Monotones 
> 
> Your Cheatin’ Heart/Hank Williams
> 
> I Wonder Why/Dion & The Belmonts
> 
> Just A Dream/Jimmy Clanton
> 
> La Bamba/Richie Valens
> 
> Rave On/Buddy Holly
> 
> At The Hop/Danny & The Juniors
> 
> Rockin’ Robin/Bobby Day
> 
> Kansas City/Wilbert Harrison
> 
> See You Later, Alligator/Bill Haley and The Comets
> 
> Til I Kissed You/The Everly Brothers
> 
> Sea of Love/Phil Phillips with The Twilights
> 
> You Send Me/Sam Cooke
> 
> In The Still of the Night/The Five Satins
> 
> Oh, What A Night/The Dells
> 
> Thank You, Pretty Baby/Brook Benton
> 
> You’re So Fine/The Falcons

#### Lawrence, Kansas, September 1947

Dean Winchester pulled at the collar of his crisp white shirt ignoring the dark looks his mother was giving him. The overly starched collar helped him ignore the half healed mosquito bites on his legs that still itched every now and then and that he continued to scratch at despite his mother’s admonishments. He looked around at the other kids and was supremely unimpressed.

Tugging at his mother’s skirt to get her attention, he demanded, “Who’s gonna help you take care of Sammy if I’m stuck here all day?”

“I’ll manage, Dean, don’t you worry. You’ll make lots of new friends and learn to read. It’ll be fine, you’ll see,” Mary said gently, shifting two-year-old Sammy in her arms. “Go on now, get in line,” she said with a subtle push.

Dean stomped away, determined not to look back. He thought he might cry if he did and there was no way he was going to let anyone see him cry. He got in line behind a skinny kid with dark, messy hair who was bravely sniffing back tears. Dean nudged him with his shoulder. “I’m Dean. Who’re you?”

The boy, dressed in an equally white and starched shirt and long dark blue cotton shorts turned watery blue eyes to Dean. “I’m Castiel.”

Dean, knowing just how Castiel felt, also knew the perfect remedy. “I’ve got a big piece of my mom’s apple pie in my lunchbox. I’ll share it with you. If you want, that is,” Dean offered.

Castiel’s eyes grew wide. “Homemade apple pie?” he asked.

“Yup. Best pie in all of Kansas,” Dean stated proudly.

“I – I’d like that.” Castiel answered.

~*~

That first day, Dean had come out excited and wanting to introduce his new found best friend to his mother. By the time the boys had finished telling Mary about their day, the schoolyard was nearly deserted and there was no one there to pick up Castiel. Mary’s lips had thinned when she heard Castiel’s name even as her eyes had softened.

Mary knew what everyone in town knew about the Novaks. They were the wealthiest family in Lawrence and had been for eight decades. They rarely mixed with anyone outside their social class and the family had grown small in recent years. When the youngest Novak, Castiel, was four, his parents were killed while on a ski holiday. Castiel was left with only his older brothers, Michael and Gabriel to raise him. They loved him, but had no idea what to do with a small child.

They had gone through a number of nannies by the time Castiel had started school. Upon questioning, Castiel confessed that his latest nanny had quit two days before and his brother Gabriel was supposed to pick him up. Mary gave Sam to Dean and told the boys to go play while she paced the now deserted schoolyard. Twenty minutes later a shamefaced Gabriel stood quietly while Mary hissed her anger into his face.

Being a man of business and capable of making immediate decisions, he hired Mary on the spot. She would be responsible for picking Castiel up from school, feeding him dinner, and overseeing his homework until Gabriel or Michael could pick him up.

It was a solution that worked well for everyone. Except John, who was unhappy about Mary having a job. They had a vicious fight, screaming in whispers, and didn’t talk for a full week until John realized that there was no real work involved and relented. He never asked her for any money and Mary carefully banked most of it for Dean and Sam.

Dean and Castiel were just happy that they got to spend more time together.


	2. Chapter 2

#### July 1948

School had been out for a week and Dean was bored. Sammy was too little to play any real games and his best friend was away for the entire summer. He spent a few minutes playing in the yard before returning to the house to see if something interesting was going on. Dean went from his yard into the kitchen and back again and again, slamming the door harder each time. Mary was doing her best to be patient, but he was getting on her last nerve.

“Come on, sweetie, let’s go to the park,” she suggested.

“I don’t wanna go to the park,” Dean pouted.

“Well, I do and Sam needs to get out,” she chided her older son. She knew he was missing his best friend. “You can’t sit at home and brood. Castiel will be back before you know it,” she said. Mary had a feeling that Castiel wouldn’t last very long in the sleep away camp his brothers had sent him to, but she wasn’t about to tell that to Dean in case she was wrong.

“It’s not fair,” he insisted, stamping his foot. “Cas didn’t even _want_ to go to camp.”

“His brothers thought it would be good for him. You know all this and you’re old enough to understand it.”

“Why couldn’t he have just stayed here?” Dean asked. 

“I don’t know, sweetie. I would have been happy to have him. Honestly, when he’s here the two of you don’t need anything except to be fed every twenty minutes or so,” she teased.

~*~

Mary got both the boys to the park and sat gossiping with the other moms under a bright shining sun and a perfect cloudless blue sky, while Dean pushed Sam on the swings. When he tired of that, they took to looking for interesting rocks. As a treat, she brought them ice cream and they were both filthy and sticky by the time they returned home.

She wasn’t all that surprised to find Gabriel and Castiel sitting on the porch when they returned from the park. Grinning slyly, she told the boys to watch out for Sammy while she and Gabriel talked.

Pouring them both glasses of ice tea, she sat silently waiting for Gabe to tell her what was going on.

“He threw temper tantrums, cried, and refused to do anything,” Gabe confessed. 

“I did tell you day camp would be a better choice,” Mary replied smugly.

“You and John agreed that it would be good idea for both of them to spend some time with other kids,” he reminded her.

“Yes, but this went in the complete opposite direction.”

“So, what do we do?” Gabe asked helplessly.

“Send Castiel to day camp so the boys can at least be together on weekends,” Mary suggested.

Shaking his head, Gabriel grinned wryly. “I’ve already offered that. He won’t go unless Dean joins him. Barring that, he’d be just as happy to spend his days here.”

“You know we can’t afford camp, Gabriel.”

“We’d be willing to pay Dean’s way. It would come out to the same as if we were paying you. You’d still have to watch him for a few hours a day and feed him dinner, so we’d be paying you for that,” he explained. “It isn’t like we can’t afford it, Mary. I know John’s proud, but this is in the best interest of his son and my brother.”

“Can we still get them in? Most camps started last week,” she wondered.

“You forget that Michael can talk the birdies off the trees,” he teased.

“Let me talk to John tonight. I think camp might be good for them both. They’d have a lot of other boys to play with,” she decided.

~*~

“How’d you do it?” Dean asked.

“I didn’t really do it on purpose. But all those other kids were boring and stupid. And I missed being at home,” Cas told his best friend. “They kept telling me I’d get over it, but I didn’t.”

“They shouldn’t have sent you when you didn’t want to go anyway!”

~*~

Two days later, both boys started their first day of camp. They came home sweaty, hungry, and anxious to tell Mary about everything they’d done. She shooed them into baths and fed them dinner, listening to their excited chatter. 

John, as expected, wasn’t thrilled, but he relented in the face of logic and the thought of giving Dean an opportunity he might not otherwise have.


	3. Chapter 3

#### March, 1952

The moment the boys walked in, Mary knew something was wrong. Both boys looked disheveled and Cas was sporting the beginnings of a black eye, while Dean’s lip was swollen and split. They were old enough to walk Sam home from school so she no longer picked them up. Sam, his usual sweet self, offered Mary a hug and chatter about what he’d done in school that day. 

Dean and Cas ate their snack in silence and began their homework with none of the usual prodding or complaints. She watched them, alert for any clues. Sam finished his homework quickly and Mary ushered him into the living room and the puzzle they’d all been working on. Sam was thrilled to get a chance to do the puzzle on his own. His small hands could never quite keep up with Dean and Cas, even if they were nice enough to let him put in the last piece.

Cas finished his own homework first and picked up a book and began reading, ignoring Dean. Every now and then Dean would look up at Cas and scowl. The tension in the room grew and Mary was no longer willing to wait for the boys to tell her what had happened. “You boys want to tell me what’s going on?” Mary asked.

“Nothing,” both boys said sullenly and in unison. They bent back to their books, once again ignoring each other.

Mary put up a pot of her extra special hot chocolate. It was a treat she saved for snow days or when one of the boys needed comfort after a difficult day. She brought a cup in to Sammy and sat down at the table with her own cup. Cas broke first, sniffing at the rich aroma. “Can I have some?”

“That depends. You ready to talk?”

Not bothering to answer, he returned to his book.

“Cas, I know you can take care of yourself! I just can’t stand by when three guys are pounding on you,” Dean burst out.

“You didn’t even give me a chance, Dean,” Cas shouted.

“Look, all I did was even out the odds a little. Two against three is just more fair.”

“I - -I just don’t want anyone to think that I need you to fight my battles,” Cas explained.

“After today, not one person is gonna think that. You’d already kicked Steven’s ass and were well on your way to doing the same to Robert. It’s not your fault Walter fights dirty,” Dean grinned.

Castiel puffed up a bit. “Yeah, I totally kicked ass,” he bragged.

“Language boys. I guess those boxing lessons John’s been giving you guys came in handy,” she acknowledged. She’d been against those lessons, but couldn’t deny they’d come in handy today. “Although, since you’re both sporting bruises I’d say some more lessons are in order.


	4. Chapter 4

#### June/July, 1953

“No,” Castiel declared, stunning Michael, while Gabriel laughed.

~*~

“Nope, not this year. Me and Cas already decided,” Dean stated to his stunned parents.

~*~

Michael immediately called John and Mary and made arrangements to meet with them. Gabriel took all three boys out to play miniature golf, giving the other adults time to talk privately. 

“Are you willing to work, Mary?” Michael asked. “I know the boys being in camp gave you a little bit of a break.”

“I have no problem with that, Michael. But, you must realize boys their age are pretty much gone all day,” she answered.

“Nothing wrong with kids their age having a little independence,” John chimed in. 

When Dean and Cas had refused to go to camp, Michael, Mary, and John had been caught off guard. After a few moments, John had gone straight to indifference. It had never sat well with him that the Novaks were paying his son’s way. It rankled that he couldn’t afford to give his sons the same advantages the far wealthier Novaks gave to Castiel.

The Novaks and the Winchesters had had any number of conversations over the years about Dean and Castiel spending so much time together without coming to any concrete conclusions. One thing was sure; there was no separating the boys. They both had other friends, but preferred each other. Not one other boy had a chance of coming between them. There was no question that their other friends were willing to follow wherever they led. 

~*~

Late last year, Dean had begun lobbying hard for a brand new Schwinn bicycle. He’d ordered the catalog, leaving it in various places his parents couldn’t miss. His talk was filled with the specs from the various bikes and he made sure to point them out whenever they were out and saw one. He wasn’t exactly subtle and while John and Mary pretended to ignore him, they had a good laugh about his behavior. John had been pulling in extra hours at the garage and they had already bought the bike, storing it at a neighbor’s house.

It was the only bike to have in Dean’s opinion. He was hoping for a Phantom, but would have been satisfied with a Panther. When he saw the Phantom waiting for him on his birthday, he fell in love with it in the way only twelve-year-old boys could. It was black with touches of red and shiny, shiny, shiny, and he loved the lines of it. He spent the rest of the day dreaming about the adventures he would find with such a cool set of wheels. Every so often, he’d go into the mudroom to caress it. The only thing that managed to get his attention off the Phantom was his mother’s pie.

Castiel, who’d known about the bike, bought Dean a saddle bag to attach to the back of it. Normally not one to pay attention to such things, Castiel was stuck with just how sleek and beautiful the bike was, and he too, fell in love. He began begging for the same one as an early birthday gift. He was fast outgrowing his own bike and he’d never be able to keep up with Dean if he didn’t have a new one. He wasn’t surprised to see it on the last day of school. Gabe had it delivered to the Winchester home and it was identical to Dean’s except for the color; Cas’ was red with black touches on the chrome. 

~*~ 

Dean and Castiel, like every other kid in Lawrence, were allowed to wander all day as long as they were back home by dark. Cas usually left his bike parked next to Dean’s in the garage, and they’d take off as soon as they’d shoveled down their breakfast. Mary always packed lunch and they both had thermoses of lemonade or iced tea to take along with them. 

Once a week, they took Sammy to the park and Mary would give Dean a dollar so they could all get a burger and fries or some ice cream and candy. Dean didn’t mind; he thought Sammy was pretty cool and he wasn’t much of a pest. Most of the kids they ran with were saddled with the same chore, so even if they had to hang out at the park on Wednesdays, most of the guys with younger brothers were also there.

~*~

There was a good sized wooded area a half mile from Dean’s house and that’s where Dean and Cas most often went. It wasn’t just a patch of woods to them; it was large uncharted territory, filled with danger, intrigue, and adventure. There were a few swimming holes all the local kids knew about. The biggest and best one was usually crowded with older kids and they didn’t want the younger kids around, spoiling their fun. There was a smaller swimming hole that wasn’t as deep, and it was more difficult to reach. The upside to that was they didn’t have to worry about girls invading their sacred male space.

Dean and Cas, more adventurous than most boys their age, had hacked their way deeper into the woods where there were no trails and found a small swimming hole no bigger than six feet in diameter. They kept this to themselves and they began work on a secret clubhouse close to the small swimming hole. They dragged found pieces of lumber through the narrow path they’d hacked out and borrowed some of John’s tools and nails.

In a little over two weeks they had a small, serviceable shelter that only the two of them knew about.

Dean had covered the shelter with branches and it was difficult to see unless you were right on top of it. “That’s perfect, Dean,” Cas stated after the last branch was in place. “It looks like it’s natural.”

“Good. I think we should roll a big rock in front of it.”

“Why?” Cas asked curiously.

“So no one else can use it. I’m gonna put a shelf in it and we could keep a blanket and maybe some books in there. It won’t last past the summer, but how cool is it to have our own private clubhouse?” Dean asked with enthusiasm. “I think it’ll even keep us dry if it rains,’ Dean boasted.

“Where’d you learn to do this stuff?” Cas demanded. 

“I dunno. I just see it in my head,” he explained as they made their way to the swimming hole. 

“You always have the best ideas,” Cas said in admiration.

Stripping off their shorts, sneakers, socks, and tee shirts, and singing “Whaaa, whaa, wha,” they plunged into the icy, dark water. The day was brutally hot and even though it was cooler in the woods, Dean and Cas were sweaty and sticky from their labors. The cold water snatched their breath away and raised goosebumps. They swam and horsed around for an hour before hunger struck hard and fast.

Climbing out of the small swimming hole, they retrieved their lunches from their saddlebags and perched themselves on one of the large rocks that surrounded the hole. They eagerly tore into their bags to discover Mary had given them each two peanut butter and jelly sandwiches and one of ham slathered with mustard and now limp lettuce along with two apples, and a half dozen cookies. 

Dean inhaled two sandwiches before he slowed down enough to taste his food. Cas, eating nearly as fast, contemplated Dean as he ate. “So, what did you mean before? When you said you saw the clubhouse in your head?”

“It’s hard to explain. I see a space and I know what would fit in it. The last time I was in the library, I saw a book about guys that design houses and buildings. They’re called architects,” Dean explained, green eyes glittering in excitement. “I think I’d like to do that.”

Cas silently digested this new information about his best friend. He was hurt that this was the first he was hearing about any of this stuff. It was also the first time that he and Dean weren’t on the same page. His older brothers had recently been making comments about Cas joining the family law firm and he’d heard John hinting that it would be good to be in business with his oldest son.

“What about you, Cas? Don’t you want to do something different than work in a stuffy office like your brothers?”

An idea had been growing inside Cas for a year or two. An idea he’d never expressed out loud. He barely allowed himself to think about it. “Michael’s already talking about Harvard Law School,” he confided.

“Fuck that, Cas! What do _you_ want to do?”

Cas laughed. They were at that age where foul language was expected among their peers. Cas had heard Dean curse often when they were with their other friends, but never when they were alone. He knew Dean felt like he _had_ to talk that way to fit in. He figured Dean must really be upset on his behalf if he was cursing when he didn’t have to. “I… I think I’d like to be a veterinarian,” he whispered.

“Really? That is so cool, Cas.”

“Do you really think so?”

“Yeah, I do.”

“Maybe… Maybe that’s what I’ll do then,” Cas said slowly, as though the possibility that he _could_ really do it had never occurred to him.

“You know what else I want?” Dean said.

“What, Dean?”

“I want to live by the ocean. I want to hear the surf and be able to walk on the beach whenever I was in the mood,” Dean confessed.

Castiel looked at Dean thoughtfully. He’d been on vacations near the ocean more than once. Dean had a personality as large as the ocean. “Yeah, I could see you by an ocean. I think you’d like it.”

“I know I would,” Dean exclaimed decisively.


	5. Chapter 5

#### July, 1954

The Novaks arrived at the Winchester home at 8 AM. Mary put out a large spread for breakfast, including Dean and Castiel’s favorites. Unfortunately both boys were far too hyped up to eat. Gabriel and Sam made up for their lack of appetite. 

Dean and Cas had entered the annual Lawrence Soap Box Derby. Usually, both families went and watched. Lawrence was a small town and like small towns across the country, there weren’t endless activities, so things like parades and high school football games were always well attended.

In January, Dean decided he wanted to enter the derby. He managed to talk a reluctant Cas into it. Michael and John met and over several beers they struck a deal; Michael would supply all the materials if John would help Castiel build his car.

Dean and Cas spent every spare moment over the course of a month designing their cars with a little help from John. They each kept their designs a secret until it was time to start building. Castiel’s car looked much like soapbox cars had always looked like; a bit like a rowboat with wheels. The front of Dean’s car was rounded, while the back was squared.

John helped them build the cars, spending an equal time with each boy, teaching them as he went along. It was something he was used to doing. He’d been teaching Dean and Cas how to fix cars for years. Sammy had been listening in since he turned eight. 

Dean had painted his car black. When it was done, he decided it needed something more and he painted eyes and a shark’s gaping, toothed smile on the front. Castiel, laughing when he saw it, remarked, “Even if you don’t win, that car will still scare the crap out of everybody.”

“That’s the idea,” Dean replied, looking over Cas’ red car. “You missed a spot.”

“Do you think we have a chance of winning?” Cas asked, dipping his paintbrush.

Shrugging, Dean responded, “Nah, but who cares? It’s gonna be fun. Richie Dearing will probably win again anyways.”

“That loser,” Cas spat out. “He never wins in Ohio anyway. Which is good because can you imagine him being even more conceited than he is now?”

Dean took a quick look around to make sure no adults were around. “He’s a pussy. The minute I’m big enough, I’m going to kick his ass.”

They both dissolved in laughter.

~*~

The day of the derby was overcast, but it didn’t keep anyone away. Amid the low roar of the crowd, the scents of hotdogs, kettle corn, cotton candy, and roasted corn on the cob permeated the air. It was an occasion to socialize with friends and neighbors. The women attempted to mind over active and excited children while they gossiped, and the men discussed sports and politics as they waited for the heats to begin.

~*~

Richie Dearing won amid the hundreds of cheering people. Castiel came in a surprising fifth place, while Dean came in third place. The Winchesters and the Novaks were waiting to congratulate the boys. They endured the hugs and slaps on the back good naturedly. 

Mary noticed a large group of pretty giggling girls waiting for their turn to congratulate the boys. She pushed Dean and Cas over to them, noting with some amusement that both boys seemed more uncomfortable than triumphant. 

When Dean and Castiel managed to get away from their admirers, both families went out and celebrated with burgers and milkshakes. The three boys drove the adults nuts by singing Sh-Boom anytime they didn’t have food in their mouths. 

Dean proudly placed his third place trophy on his shelf and fell asleep dreaming of sleek black and red cars that roared over pavement so fast they blurred.


	6. Chapter 6

#### May, 1957

‘The Book of Love’ was playing on the juke at top volume. Beef Burger Bob’s was packed to the rafters with people coming and going. The grill was working overtime to keep the hungry teens fed and the soda jerk was moving as fast as he could. The two busboys were kept busy cleaning up as each table finished eating and moved to the back where the jukebox was so they could dance and socialize. On Friday and Saturday nights, they didn’t bother with the cheap red checked tablecloths and the harsh lighting was reflected off the light colored wood of the tables. Pastel pink and blue walls made the place look larger, but everyone in town knew Bob’s was dangerously overcrowded on Fridays and Saturdays.

Dean and Castiel were holding court. Last week, Castiel, as captain of the baseball team had brought home the championship by pitching the third no hitter game of his career. He was the current star of their social group. Dean had had his turn when he’d made the winning touchdown of the season, giving the team their third straight championship win.

They usually showed up at Beef Burger Bob’s once a week, depending on their game schedules, but for now football and baseball were over for the year. It was the only time they really gave themselves a break; Dean was studying his ass off in the hopes of getting into a decent school. As the captain of the football team, he was pretty much guaranteed a scholarship, but he didn’t want to count on it and had decided to keep his grades up as insurance.

He, John, and Cas were also restoring the 1953 Chrysler Imperial John had picked up for a song. By the time they were finished, it would be like the car had just rolled off the factory line. Dean was just as excited about the Imperial as he’d been about the Phantom. He’d decided to paint it eggplant purple. 

Cas always had access to one of the family cars and he’d been promised his own car as a part of his graduation gift. Michael was hoping the independence of his own car might put some distance between Castiel and Dean. He was concerned about his little bother and was unhappy that he seemed to have no interest in the family law firm or in law at all.

The Winchesters and Gabriel had never bothered to tell Michael that Cas had been working for John alongside Dean, doing small car repairs. Cas was very proud of himself and he saved every dime he earned. Michael would have been appalled about Castiel doing manual labor.

Hank Williams’ plaintive voice was now singing ‘Your Cheatin’ Heart’ when the gaggle of girls made their way to Dean and Cas, most in wide skirts for ease of dancing. They all wore saddle shoes.

“Hi Dean! Hi Castiel!” they giggled.

“Hi,” Cas answered.

“Hey, ladies,” Dean flirted.

“Did you want to dance?” Rebecca asked Dean. She’d warned all the other girls off Dean before they’d approached.

“Maybe later,” Dean replied taking a huge bite of his burger. He could think of a hundred other things he’d rather do than dance with Rebecca and hoped his bad table manners would put her off. He didn’t have the time in his life for a steady girlfriend and Rebecca had been angling for that position since eighth grade. 

Huffing at the rejection, she turned to Cas just as ‘I Wonder Why’ was starting to play on the jukebox. “What about you, Cas?”

“Sure,” he replied, rising to join her. The other girls followed knowing that Rebecca would only stay on the dance floor for a few minutes in an effort to make Dean jealous. Cas was just as popular with the girls and he didn’t play favorites. He liked to dance and would dance with all of them if they wanted.

On the way home, Dean and Castiel discussed their summer plans, pushing all thoughts of school and girls out of their minds.


	7. Chapter 7

#### August, 1958

The Imperial slowly cruised Mass Street. Cas was riding shotgun and two giggling girls were in the back seat. They were the girls of the month and they intended on taking full advantage of their time with the two most popular boys in school. 

Dean and Cas dated a lot, but they never had girlfriends for long. They’d either get bored of the girls after a few weeks, or the girls, often angling for more became frustrated and angry. It didn’t help that Dean and Cas always insisted on double dates.

It was a hot Saturday night and every teenager in town was either cruising or hanging out in groups along Mass Street. Occasionally a car dropped out of line to take a burger break or the go to the local make out spot. Cas didn’t see the point of cruising; it generally bored him after a few times up and down the street. If they were between girlfriends they’d grab a burger and then find something else to do. Now, one of the girls, Lorraine, was whining. “This is boring. Let’s go make out.”

His date, Nora, trailed her hand through his hair. “I agree. We should go make out.”

Cas caught Dean sneaking a look at his watch and decided to do the same. It was now 10:15 PM. It would take another fifteen minutes to escape the traffic on Mass Street and ten minutes to get to the local make out spot. The girl’s had an eleven thirty curfew and it would take twenty minutes or so to take them home, giving them thirty minutes to make out.

~*~

Lorraine was climbing onto Dean’s lap. “Hey, we don’t have time for that, and we aren’t alone,” he reminded the petite blonde. He looked at his watch. “We’ve got to get going anyway if you want to get home by curfew.”

“You don’t have to be such a gentleman, Dean. If we were going steady, my parents wouldn’t care if I broke curfew. We’re both going to be seniors soon and lots of couples get married right after high school,” she informed him.

“This is our second date and you’re talking about going steady?” he asked incredulously and with no small amount of horror. He completely ignored the marriage part of her statement. “You’re a nice girl, Lorraine, but I’ve got football and I have to maintain my grades and I want to go to college,” he listed.

“I’m sure Daddy would give you a good job at the bank,” she offered.

He laughed, “Yeah, no thanks.”

“I’d like to go home now,” she huffed, near tears.

~*~

They dropped the girls off and drove around silently until Dean had blown off his bad mood. “Seriously, what the fuck is wrong with the girls in this town?” Dean bitched.

“Well, you’re the most popular guy in school and going steady with you would be the ultimate achievement,” Cas explained.

“I’ve got plans, Cas. I’m not going to live and die in Lawrence fucking Kansas,” he vowed. “What about you, why don’t they pull that shit with you? You’re just as popular as I am.”

“My family’s reputation,” he said simply. “There isn’t one girl in Lawrence that thinks I’d marry them. They all expect me to go to Harvard or Yale and marry some society girl.”

“Lucky you,” he said sarcastically. “I’ve got another year of dealing with this bullshit.”


	8. Chapter 8

#### June, 1959

The red and white Dodge Coronet’s brakes squealed in front of the neat two-story home. Castiel jumped out of the car, a huge grin splitting his face.

Sam got out of the rocker, his big feet managing to trip him just a bit. “Cas! Gabriel gave you the car?” he shouted.

“Yup. I finally wore him down,” Castiel replied.

“I’m calling dibs on riding shotgun!” Sam called out just as Dean stepped out the front door.

Dean smirked as he caught Cas’ eye. “Sure, Sammy. I’m sure Cas won’t mind letting you ride shotgun. Once,” he drawled. 

Cas walked up the front steps leaving Sam to drool over the car. “Did you tell them yet?” Castiel demanded.

“Nope. I’ve been waiting for you. I figure my dad won’t blow a gasket if you’re here.”

Cas looked his friend over critically; Dean looked freshly scrubbed, his hair perfect and so unlike his own messy mop, his jeans neatly pressed as was his short sleeved button up. Incongruously, his feet were bare. “Whatever you do, don’t lose your temper, Dean.”

“I’ll try, but I’m not making any promises, Cas. The old man knows just how to get under my skin,” Dean groused.

They walked into the house together; John was pouring over the newspaper, a sweating bottle of beer leaving rings on the pristine kitchen table. Mary was at the counter preparing tuna salad for lunch. Dean opened the fridge and pulled out two Cokes. He opened them, handing one to Cas and joined his father and friend at the table.

“Can I talk to you guys for a minute?” Dean asked.

Wiping her hands, Mary turned immediately to her oldest son. “Something wrong, honey?” she inquired, a slight catch in her voice that only John heard.

Dean rubbed the back of his neck, a sure sign that he was nervous. “No, it’s actually good news,” he answered.

He fished the letter he’d stuck in his back pocket out and looked his father in the eye. “Iowa State wants me to play football for them. They’re willing to pay my way. Cas got in also,” he added, hoping that would help sway them.

Dean knew his father had been making plans to open his own garage and he needed Dean’s help. But the last damn thing Dean wanted was to be was a mechanic.

“Dean, I thought we agreed that you’d help me get the business off the ground!” John said loudly.

“No, Dad. You talked and I didn’t disagree with you.”

“Well, that’s the same thing as agreeing,” John argued.

“No it isn’t,” Dean insisted. “You’ve got my whole life mapped out and didn’t bother to ever ask what I wanted!” Dean shouted.

Mary put her hand over John’s, silencing him. “What _do_ you want, Dean?” Mary inquired softly.

“I’m planning on studying architecture,” Dean answered, his chin thrust out in defiance.

John snorted and locked eyes with Dean. “You don’t really expect to earn a living with that, do you?”

“Yeah, Dad, I do,” he answered, his green eyes pleading with John for understanding.

“I hope you don’t expect me to support you,” John countered.

“Any support Dean needs, he’ll get from me,” Mary answered before Dean could. “I’ve got enough set aside for both him and Sam.”

Dean raised grateful eyes. “Thanks, Mom. I doubt you’ll have to give me much. They said they’d pay for school, housing, and food. Cas already has an apartment and the school is gonna pick up my share of the rent,” Dean explained. “Plus, I’ve also got some money saved.”

“Why not U of K?” John suddenly demanded. “You too good for the local school?”

“Their offer wasn’t as good,” Dean said. It was true. Almost. Since he lived a short drive away from the campus, they hadn’t offered him housing or a full meal plan. It wouldn’t have mattered if they did. It wasn’t that Dean felt he was too good for the local University, but he had to leave home. He knew if stayed in Lawrence, John would twist him all up until he was stuck in a life he didn’t want. He had to leave to live the life he wanted.

John grunted in reply, his fingers worrying the label on his beer. 

“There’s one other thing,” Dean began sheepishly, his hands scrubbing at his face.

“Boy, you better not have gotten some girl in trouble,” John spat.

Blushing, Dean said, “Jeez, Dad, you don’t have a whole lot of confidence in me, do you?”

Mary glared at John. “That’s enough, John. What is it, Dean?”

“Cas and I are going on a road trip before school starts,” Dean explained.

Glaring once more at John, Mary turned to Castiel who had remained quiet during the brief family argument. It was what he generally did when Dean and John went head to head. He’d had a lot of practice over the years. “Dean said you also got into Iowa State. Are you still going to study veterinary science, dear?”

“Yes, I am, eventually. I’m going to be taking all the same classes that would be required for pre-med. Michael is just as upset as we knew he’d be and Gabriel thinks it’s hysterical,” Cas answered. “But you always told me to follow my dreams, Mrs. W,” he added slyly.

“So I did,” Mary noted. “And did you get a scholarship as well?”

“I did. Not that I need one, but I plan on using the money I would’ve spent on school to open up my own practice.”

“That’s wonderful, Cas. We’re very proud of both of you. Aren’t we, John?”

“Sure,” John allowed.

“Tell us about the road trip,” Mary demanded.

“We’re going to Florida. Kind of a last hurrah before school starts,” Dean enthused. “As part of Cas’ graduation gift, Michael made a two week reservation for us at the Eden Roc Hotel in Miami Beach. We figure we’ll take a week or so to drive down there and maybe do some camping on the way. I always wanted to see the ocean.”

“Just how long have you been planning this?” John demanded.

Laughing, Cas answered. “Since seventh grade maybe?”

“Michael also got him a new Nikon F, so we can take lots of pictures. It’ll be almost like you were with us,” Dean added to further convince them. 

“Can I go with them?” Sam whined. He’d walked into the kitchen as Dean was telling his parents about going to Florida.

“No!” John and Mary said in unison.

“Oh, come on! It’ll be just like ‘On The Road’,” Sam complained.

“You wanna go on the road, you’ll start saving up like your brother,” John snapped. He rose and got two beers out of the refrigerator. He opened them and handed one to Dean and one to Castiel. It was his way of letting his son know he was now a man.

Dean took his beer with only a little smirking and drank deeply. It turned out to be one of the best beers in his life.


	9. Chapter 9

#### Several Days Later

Michael and Gabriel took Castiel and the Winchester family out to dinner shortly before the boys were set to leave. Although the two families had been forced together through circumstance and the friendship between Dean and Cas, Michael and John both resented it. Neither of them had ever made much of an effort to hide how they felt, although Michael was more accepting of the relationship than he had been in the past. If either John or Michael knew how close Gabriel and Mary had become, they would’ve been very unhappy.

John wasn’t thrilled that he’d had to get dressed up simply to have dinner. Unfortunately, Teller’s Restaurant had a dress code that included a tie and jacket for the gentlemen. He kept picking at his collar, until Mary put a stop to it with a well timed glare.

Michael ordered a bottle of wine for the table and a beer for John before having a brief conversation with the waiter. “I thought we’d eat family style if that’s okay with everyone” Michael suggested. “Antipasto, linguine with white clam sauce, baked clams, and veal parmigiana.” 

“That sounds wonderful,” Mary said.

“I hope you intend on ordering double portions for Sam,” Gabriel teased the youngest Winchester. It was an ongoing joke that Sam’s appetite was out of control along with his seemingly endless growth spurts.

“Ha-ha, Gabe,” Sam replied, blushing. 

Michael signaled the waiter with a nod. “What time do you boys plan on leaving,” Michael asked.

“We figure we’ll hit the road as early as possible,” Dean answered for them both.

“And you’ll be checking the car one last time tomorrow, John?”

“Yeah, although I expect I’ll find everything in good order,” John replied. Grinning, he turned his attention to Gabriel. “You do maintain your vehicles, Gabe, I’ll give you that.”

The antipasto arrived and conversation halted as two waiters plated the food from a large dish. When they’d all been served, they began eating. 

“So, Cas, I know you and Dean are going to hear this all day tomorrow from John and Mary, but you’re going to have to hear it from me as well,” Michael started. “You boys need to be careful and keep your noses clean. I expect you to call at least once a week,” he continued.

Reaching into his pocket, Michael withdrew an envelope and handed it to Castiel. “I’ve given you a list of business contacts from here to Florida. If you get into any kind of trouble, give one of them a call and they’ll take care of you until one of us can get to you.”

“Thanks, Michael. We’re not looking to get into any trouble, but it’s good to be prepared,” Cas said tucking the envelope into his suit jacket.

“What do you boys have on tap for tomorrow?” Gabe wanted to know. “Other than checking out my nearly cherry car?”

Cas turned bright blue eyes to his brother and said innocently, “Well, Mrs. W promised me French toast for breakfast. We’re still debating lunch. I’m leaning toward mac and cheese, but Dean is holding out for burgers and potato salad. And there’ll be fried chicken and mashed potatoes for dinner, so I’d say a lot of eating.”

Gabe immediately pled his case with puppy dog eyes.

Mary laughed, “You know the rules, Gabe… If you expect to eat, you have to help.”

Both Dean and Cas choked back laughter; they remembered the last time Gabe had “helped.” Mary had ending up chasing him through the house brandishing her second best wooden spoon.

“I’ll make you a deal – throw in a pie and I’ll hire a housekeeper for the entire day. We’ll help you cook and she’ll do all the cleaning,” Gabe bargained.

“Deal,” Mary agreed, sticking her hand out for a shake.

“Michael, I won’t be at work tomorrow,” Gabriel said.

The entire table laughed.


	10. Chapter 10

#### Friday, June 26, 1959: Day One

Dean and Castiel woke early, anxious to get on the road. They were surprised to see John, Mary, and Sammy up with them. Mary was heating the extra French toast she’d put aside yesterday and scrambling up eggs and bacon. She’d already packed up enough fried chicken and potato salad so the boys could travel all day without stopping for food. She also gave each of them a thermos of coffee prepared they way they preferred.

As they’d packed the car the night before, there wasn’t much to do other than eat. That was accomplished in the only way two healthy teenaged boys could; quickly. The sun was just beginning to rise, painting the sky a dozen shades of orange with bright yellow steaks in a dazzling display. The sun would soon burn off the few clouds and the heat of the day could already be felt. The small family followed Dean and Castiel out to say goodbye.

John grabbed his son in a hearty hug, then stepped back and pressed some bills into his hand. “You be careful, boy. And call. Don’t make your mother worry,” he ordered.

Surprised by the gesture, Dean grinned. “Yes, sir. At least once a week. Thanks, Dad.”

“You sure I can’t go with you?” Sam asked once again.

Dean ruffled the boy’s hair. “Nah, you gotta stay home and take care of the folks,” he teased. He grabbed Sammy up in a hug, and whispered, “You’ll get your turn, I promise.”

Dean watched as Sammy sniffed back tears and went to join his father who was now saying goodbye to Cas. His mother had already hugged his friend tightly, whispering her goodbye in his ear. Dean watched his dad shake Castiel’s hand and give him a one armed hug. 

Mary put the fried chicken and potato salad in the car and was now sneaking one more blanket in the trunk. She looked up and met her son’s eyes and blushed. Chin thrust out, she said, “If you have to camp, you’ll be happy. It gets damn cold at night.” She then handed him her old Kodak Retinette. “I thought you’d like to take some of your own photos,” she said.

Dean hugged her and swung her around. “You’re right, Mom, thanks. For everything.”

“Put me down,” Mary demanded, laughing. When Dean had set her on her feet, she cupped his face. “I love you, baby.”

“I know. I love you too, Mom.”

She hugged him fiercely. “I want you to remember something, Dean. When you find something you love, grab onto it with both hands and never let go. It doesn’t matter what anyone else has to say about it.”

“That’s what I’m doing, Mom. Just like you taught me,” Dean replied earnestly.

Mary gave him a strange look, one Dean had never seen before. “You just think on that, son. And don’t ever forget that I’ll always love you, baby.” 

Goodbyes done, Dean joined Cas in the Coronet. He started the car while Cas fiddled with the radio station. John slapped the roof and the boys were off.

~*~

Dean navigated Lawrence quickly and his foot was heavy on the gas once they hit the highway. Cas had the map of Route 50 spread out across the dash and was diligently tracing his finger over state lines and through intersecting roads towards their destination. He spared a glance over at Dean and grinned. There were few things in life better than the freedom of the open road and the company of his best friend. The speedometer’s slender arrow was hovering over eighty, and the car was all but flying over the smooth expanse of tarmac.

They’d rolled the windows down soon after they departed, and the wind was roaring through the car and making the edges of the map flutter and flap. Castiel finished tracing over their route and he relinquished his hold on the map in an attempt to fold it, but the wind blew it out of his hands and it ended up plastered over his face. Dean’s resulting chuckle had Castiel laughing along as he peeled the map off of himself and finally managed to fold it and place it back in the glove compartment.

The radio was playing and they sang along, relishing the first real freedom they’d ever had. “Hey, Cas. Let’s stop at the State Fair in Sedalia.”

“That’s not even a hundred and fifty miles away, Dean”

“Yeah, but we’ve got almost a week to get to Florida and if we have to, we can drive straight through,” Dean rationalized. “Besides, I’m in the mood for a corn dog or two.”

Cas grinned at his friend. “Always ready to eat, aren’t you?”

“I sure am. “Besides, I’m in the mood for a roller coaster ride or two. We’ll just stay for a couple of hours.”

“Sounds good. I could probably put away a dog or two.”

~*~

They found the Midway by following the roar of screaming, excited kids and parents calling them to order. It meant passing the animals and the smell of manure was sharp and pungent. Beneath the roar of the crowds and the competing pitches of the Barkers, they heard the guest singer, Gene Autry yodeling for all he was worth.

The Midway was jam packed with rides and food booths. They’d packed as many rides as they could in the designated area, making it hard to walk from place to place because of the dense crowd. Dean waved his arm expansively. “What first?”

Castiel looked around. “The Hurricane, the roller coaster twice, the double Ferris wheel and then the big one. And let’s eat after The Hurricane and the roller coaster,” he suggested.

~*~

They ended up on each ride twice except for the roller coaster, which they rode four times. Dean managed to eat four corn dogs and Cas three. They were sorely tempted by the various games, but didn’t want to end up with cheap stuffed animals. They were back on Route 50 three hours later.

They studied the map to decide how far they’d need to drive. Having some familiarity with State Fairs, they knew they wouldn’t find a place to stay within a hundred miles of Sedalia. They also didn’t want to go to St Louis and waste money on an expensive hotel. Camping was out as heavy rainstorms were expected overnight. They decided to head for Hermann.

They hit more traffic on 50 as people were leaving the fair and it took them nearly three hours to reach Hermann. They pulled over at the first motel they saw; Aunt Mabel’s. It was aging and plain but looked clean enough and they hoped there would be a room available.

The front desk was empty, so they rang the little bell. A short round man in his sixties came from the back, wiping his mouth on a large cloth napkin. They’d clearly interrupted his meal.

“What can I do you boys for?” he boomed.

“We’d like a room,” Castiel said.

“You boys know the State Fair’s open, right?”

“Yes, sir, we do,” Dean nodded.

“All my rooms were booked months ago, fellas.”

“Can you suggest something nearby?” Cas asked. “We’re tired and dirty, so we’d prefer not to sleep in the car.”

“Tell you what boys, my Aunt Mabel started this place and she’d be real upset to turn away you kids. I’m Henry Boyer,” he introduced himself. “I had a bunch of good ole boys here the other day and they trashed one of my rooms but good. I can let you have it at half price,” Henry offered.

“Does it have hot water?” Dean wanted to know.

“It does. The bed frames were all busted up along with the heating unit, so you might get cold, but I’ll give you extra blankets. You’ll have to put your own sheets on since my daughter Lori went home already, but I’ll throw in breakfast,” he bargained. 

“We’ll take it,” Dean decided.

Mr. Boyer handed them the room key, towels, sheets, pillows, and several thin blankets. They quickly made up the Queen size mattress on the floor, and Dean went to retrieve their sleeping bags, the extra blanket Mary had thrown in at the last minute, and the fried chicken and potato salad. He sent her a silent thank you. The winds had picked up since they had pulled into the motel and Dean felt the first fat drop of rain as he entered the room.

Cas had laid out the thin, scratchy blankets on top of the mattress hoping they would provide some warmth. They ate standing up, eating their fill of chicken and potato salad, then took brief showers. Shortly after they’d put on their pajamas, the power went out and they could feel the temperature in the room drop as the storm outside raged. 

They crawled into their sleeping bags, shivering. Dean threw the blanket on top of them both, but the room was cold and getting colder. Dean could hear Castiel’s teeth chattering. “Scoot on over,” he said.

Too cold to protest, Cas did. The room was heavy with silence. In the darkening gloom, Cas asked, “Hey, Dean, have you ever, y’know, did it?”

It took Dean a long minute to answer. “Yeah, twice.”

“When?” Cas said curiously. They were practically attached at the hip and he couldn’t think of when Dean would have had the opportunity.

“You remember the last time you went skiing with Michael and Gabriel?”

“Yeah, the first week of January.”

“I met this girl from Andover who was visiting her grandparents and we did it,” Dean disclosed.

“What was it like?”

“Honestly?” he began. “Disappointing,” Dean whispered in shame. “What about you?”

“No. I - - I’ve gotten to second base plenty of times, but…” Cas stopped.

“But what, Cas? You know you can tell me anything.”

“It was sort of - - gross,” he admitted. 

“Yeah, it sort of is,” Dean laughed. “You like kissing though. I’ve seen you kiss enough girls.”

“Yeah, I like kissing. But I’m not usually thinking about the girl when I’m kissing her,” he confided. 

“Who…?” Dean asked breathlessly.

Castiel heard the catch in Dean’s voice and allowed himself to hope. “Well, for the last two years, it’s been… you.”

“I went all the way with that girl ‘cause I was starting to think there was something - - wrong with me,” Dean confessed.

“I guess maybe the same thing is wrong with me.”

Dean took a deep breath. “I really want to kiss you, Castiel.”

Fumbling a bit in the dark, they found each other by touch and pressed their lips together softly. Both reaching for more, they sealed their mouths together, both of them soon pushing and grasping, taking what they wanted.

Panting, and urging Cas to open for him, Dean rolled on top of Cas, desperate for the taste of him. They kissed and kissed and it wasn’t enough. Dean pulled away and got himself out of his twisted sleeping bag and hauled Cas out of his.

Pushing aside the bags, they crashed together in the dark, with only two thin layers between them. Dean could feel an answering hardness , hear Cas’ harsh, sobbing breaths, smell the clean, masculine scent of the body beneath him and he tore at their pajamas. 

Cas’ hands seemed to be all over him at the same time as he thrust against Castiel’s lean, muscular body. It shouldn’t have been so hot. It was just two bodies rubbing and pushing against each other, but neither of them had ever been so turned on. Everything that had been missing with the girls they dated and kissed and touched was here. Everything that had been wrong now felt right and perfect. 

Castiel’s hands found the globes of Dean’s ass and held on for the ride. Their bodies dewed with sweat and they slid against each other, cocks aligned and throbbing. Cas came first and the feel and scent of semen threw Dean over the edge he’d been riding.

Their breathing and heartbeats slowed as they held each other. Dean zipped the sleeping bags together and they climbed in, still touching and stroking. “We never do things by half, do we, Cas?” Dean chuckled.

“I guess we don’t. I take it that wasn’t disappointing?” Cas asked, looking for reassurance.

“It was anything but, Castiel. I sorta wish I’d kissed you a couple of years ago.”

“You and me both.”

“I’m starving,” Dean growled. “How about you?”

“I could eat,” Cas agreed. “We still have chicken left.”

“Cool! Good thing my mom knows us so well.”


	11. Chapter 11

#### Saturday, June 27, 1959: Day Two

Dean and Cas awoke to a beautiful early summer day. Last night’s storms had blown away and the day promised to be warm and sunny. Henry Boyer welcomed them into his kitchen for their promised breakfast. His daughter was busy at the stove flipping pancakes and scrambling eggs and sausage patties.

Henry’s appetite was nearly as good as Dean and Castiel’s. Lori was amused as she made pancakes as fast as the men could eat them. “Lordy, I forgot how much teenage boys eat,” she said. 

“Your pancakes are almost as good as my mom’s,” Dean complimented her, “But your sausages are the best I’ve ever had anywhere.”

She tipped more sausage into the frying pan. “Thank you, I make them myself. I’ll just fry up some extra for you boys to take on the road.”

“That would be appreciated,” Cas thanked her.

“Where are you boys headed today?” she inquired.

“Well, eventually to Liberty, Indiana by way of Illinois,” Cas answered. “We’ll pick up Route 27 and it’s a straight run to Florida from there.”

“That’s about 400 miles, give or take,” Henry interjected. “You’ll have time to make a few stops if you like. You can go take a picture with the Popeye statue and you’ll be passing close to Oz Park.”

“Oz Park?” Dean mumbled.

“Oh, Dad, Oz Park is for little girls. I doubt these boys want to see the recreation of The Wizard of Oz. Do you like Superman?”

“Yes, Ma’am,” Dean and Cas answered together.

“Besides the Popeye in Illinois, there’s a big Superman about fifty miles out of Liberty. I think that’d be much more to your liking,” Lori advised. 

Dean and Castiel couldn’t help but agree.

~*~

They thanked their hosts, being especially generous in thanking Lori for the sausage sandwiches. They decided to go straight through Missouri, about a two hour ride. They were excited just to be on the road and weren’t in any particular hurry. They were hungry for adventure and new places and strange sights.

US Route 50 passed through rural towns and farm country, scenery they were very familiar with from their own hometown. The siren song of small towns called to them, weaving familiar fingers through them.

They could have stopped at any of these small towns and found like minded people; those who’d grown up with small town amusements and boredoms, where football was king, but if you played baseball that was also okay. There was always a burger joint or a soda shop or an ice cream parlor where the older kids hung out on Fridays and Saturdays and danced and then went to the local make out spot. Dean and Cas could have probably found the still wild patches of land where the younger kids spent long summer days exploring, dreading the coming school year, which would curtail much of their freedom.

Life in these small towns was coming to an end, though neither Cas nor Dean could have known it. They still had a decade or so of vibrant life, but small town America was in the twilight of its life. A storm was coming, a storm of such strength and upheaval that even in the midst of such change, people would attempt to deny what was happening as they tried to hang on to the last gasping breaths of these small towns.

Years later, those who’d never known small town life would mourn its passing, never pausing to think about the ugliness the prettiest of towns held. But for now, Dean and Cas were happy with the familiarity. It anchored them, especially in light of the discoveries they’d made just last night.

They reached the bronze statue of Popeye about an hour into Illinois. There were a dozen or so other people, mostly families who’d also stopped. Dean walked around the six foot high platform, staring at the six foot high bronze Popeye. Green eyes twinkling with mirth, he dryly remarked, “I thought he’d be a bit bigger.”

“Shh. The kids think he’s huge,” Cas laughed. They waited their turn and took a few obligatory photos, cracking wise and cracking up until they were doubled over.

The mothers shot them dirty looks while their husbands chuckled at their antics, remembering their own youth. They went back to the car and ate a few of the sandwiches, savoring the homemade sausage. Cas took over driving. “Hey, find a place to stop. I’m thirsty and we can get some gas,” Dean demanded.

Fifteen minutes later, they were in another small town. The gas station had a Coca Cola machine. Dean bought four cokes, handing two to Cas and drinking them down quickly. Cas drank just as thirstily and Dean swallowed hard as he watched Castiel’s throat working. Pulling his eyes away before anyone could notice him staring, Dean got in the car and found some music.

They drove another two hundred miles, finishing the sandwiches before they found the giant Superman. He stood in the middle of the Town Square, red cape billowing and hands fisted on his hips. He was at least twenty feet tall. “Now this is worth stopping for!” Dean declared in glee. They ran around the statue, taking pictures of each other. A matronly woman, still pretty in a faded way smiled and asked if they wanted a picture together. They did. She took several photos with each of their cameras.

“Thanks,” Cas said. “Is there anywhere good in town to eat?”

“You like meatloaf, mashed potatoes, and gravy?” she asked.

“I think we could manage a slice or two,” Dean admitted.

“Just up the block Regina’s Kitchen makes some good rib sticking food. And her pie is made fresh daily,” she informed them.

Cas rolled his eyes when Dean smacked his lips at the mention of pie. “That sounds good. Thanks again,” Dean said, already pulling Cas towards Regina’s. The place was crowded, but Dean and Cas didn’t mind sitting at the counter. They ordered the meatloaf blue plate specials and it was as good as advertised. The pie of the day was cherry and it came with a choice of toppings; a scoop of vanilla ice cream or freshly whipped cream. They both opted for the whipped cream.

The waitress serving them was a pretty woman in her early twenties, who despite her flirting with Dean and Cas, managed to look bored by life. Dean flirted back and that had earned them extra large portions of meatloaf and pie.

Thinking ahead, Dean ordered three meatloaf sandwiches to go. He had plans that didn’t involve looking for food to eat. He only hoped the sandwiches were as generously portioned as the rest of their meal had been.

Cas offered the keys to Dean, but he refused. There was only another fifty miles or so before they reached Liberty and Dean was looking for a particular kind of motel. He didn’t want to divide his attention.

The last portion of US 50 was empty and the Coronet ate up the miles. They were two miles out of Liberty when Dean instructed Castiel to pull into the parking lot of a place called Freedom Bungalows. 

“I thought you wanted to get to Liberty,” Cas noted even as he turned as instructed.

“I don’t know what kind of motels they’ll have,” Dean explained.

Shrugging, Cas figured Dean must have a good reason. He sang ‘You’re So Fine’ along with the radio, foot tapping, as he waited for Dean.

Wearing a goofy grin, Dean hopped into the car. “Drive around to the last bungalow. The place is pretty empty, but I told the owner that you snore like a truck driver and we didn’t want to bother anyone.”

“Neither one of us snore.”

“Yeah, but he doesn’t know that. ‘Sides, I’ve got plans and I don’t want to gag you. Although…”

“Although, what?” Cas demanded.

“I wouldn’t mind if you wanted to gag me. At least with your hand. That might be a real kick,” he leered as Cas rolled his eyes.

They grabbed their suitcases and the bag of food and opened the door to the last bungalow, switching on the lights. Dean dropped his suitcase and placed the food on the dresser, pushing Cas towards the closest bed. He gave him a light shove and joined him, taking him in his arms, kissing him.

Cas wound his arms around Dean returning the kiss enthusiastically. “Christ, Cas, I’ve wanted to do this all day,” Dean murmured between nibbling love bites. 

“All day?” Cas whispered.

“Yup. It’s just about all I’ve thought about. Well, this and food, but mostly this.”

Cas laughed, blue eyes shining. “Let’s get into a shower. We both stink.”

“In a minute. I like the way you smell. And I want to lick your nipples,” Dean admitted, stripping Cas’ shirt off. He bent his head, flicking his tongue at the small nubs, which hardened and peaked. 

“Shit, Dean, that feels so damn good,” Cas moaned. 

“I love that your body is hard. You’re a sexy bastard, Novak.”

“Not as sexy as you, Winchester. Not nearly.”

“Let’s go get wet and sweat,” Dean suggested.

They stripped, dropping their clothes in a pile, and adjusted the water temperature before stepping into the shower. They quickly took turns washing their hair. Dean unwrapped the soap and began washing Castiel.

Neither had ever showered in such intimacy before; showering with their respective teams after games was more about horseplay and getting clean. This was the complete opposite. Dean stroked Castiel’s body, learning how to touch him to maximize his pleasure. They were both hard and aching.

Dean soaped up his cock, sliding it into the crack of Castiel’s ass. He reached around with the soap and soaped up Cas. Playing with his balls for a while, rolling them, he finally took Cas in hand, jerking him slowly, twisting his hand on the fat head of his cock.

“Tell me if something doesn’t feel good, okay?”

“Jeez, Dean, everything you’re doing feels amazing. Don’t stop.”

Cas pushed himself through Dean’s soapy hand, pushing back against the hardness sliding through the crack of his ass. He threw his head back, resting it on Dean’s shoulder.

Dean’s other hand hugged Cas’ body close. “Tighten up around me,” he panted. 

“Harder, Dean. I’m so close.”

Cas tightened his ass around Dean’s thick throbbing cock, while Dean tightened his hand around Cas. Gasping and sobbing, they rode the edge of ecstasy until they could hold on no more. Cas came, spraying the wall and shuddering in Dean’s arms. Dean growled as he came, reigning in the urge to bite at Cas’ neck, his body pumping without restraint.

“God, Cas. You’re perfect.”

They rinsed off, wrapping towels around themselves. Cas fished the laundry bag out of his suitcase and stuffed their dirty things in. They’d taken enough clothes to last at least until they got to Florida, where they could have the hotel do their laundry. Dean grabbed their sun tan oil and an extra dry towel not wanting to spill oil on the sheets. Not bothering with pajamas, they climbed into bed, wanting more; more sex, more of each other, more skin, more everything. 

They lay on their sides, facing each other. Dean poured some of the oil in his hands and grabbed both their already hardening cocks, pumping slowly. The urgency they’d felt before had abated. There was now time for long, slow, luxurious tugs, and kissing, languid and deep, their tongues tangling.

Dean jerked them both to orgasm, his hands sure and knowing. They lay in the aftermath, holding each other, relaxed and energized at the same time. “Dean?”

“Yeah?”

“Do you want to be inside me?”

“At some point, I like to try, yeah, but I really want you to be inside me.”

“Do you… know how? The mechanics I mean,” Cas asked.

“You know Mark Johnson, right?”

“He’s the half back that graduated last year.”

“That’s him. On the bus ride back from our last away game, he started telling us about how he screws his girlfriend. She was terrified of getting pregnant, so he talked her into letting him do her up the ass,” Dean recalled. “He was - - very detailed in his explanation, so, yeah, I know what to do.”

“I’m don’t think I’m ready for that yet,” Cas confessed.

Dean sat up. “Cas, we’re never gonna do anything you aren’t comfortable with. I’m not ready myself. How about we learn all this stuff together? Just like we’ve always done.”

“I’m having a lot of fun learning,” Cas laughed. “And, I’m starving.”

“Hey, that’s my line! Dean complained. “Aren’t you glad I thought ahead?”

“You always have the best ideas,” Cas agreed.


	12. Chapter 12

#### Sunday, June 29, 1959: Day Three

They woke early, eager to get on the road. Driving into Liberty, they stopped at the first luncheonette they saw and ate a hearty breakfast of omelets, double orders of hash browns, double rashers of bacon, and good strong coffee. 

Dean took over the driving and got them out of Indiana and into Kentucky in under an hour. Traffic was non-existent and the scenery on US Route 27 was very much the same as they encountered on US 50; small towns, farms, and a two lane road. Cas took particular notice of the horses once they’d crossed into Kentucky.

Cas kept fiddling with the radio looking for some rock and roll. Every time he found a station, the signal kept fading in and out. They resigned themselves to country music although it wasn’t a favorite for either of them. Right outside Paris, Dean pulled over laughing. On the side of the road there were several large dinosaurs towering over the landscape.

“Grab the cameras, Cas. I’m gonna ride one of those bad boys,” he laughed.

While Cas grabbed both cameras, Dean rooted around in the trunk for a length of rope he stashed when he helped pack up the car. Cas took one look at the rope and broke down laughing. When he was able to talk, he berated Dean half-heartedly. “You are _not_ going to lasso a dino.”

“I sure as hell am. And then I’m gonna shimmy up the rope and sit on it. And then it’s your turn, buddy.”

“If we get arrested, I’m not going to forgive you anytime soon. Just so you know.”

“Take a look around. It’s Sunday, everybody’s in church and then they’ll be at the local diner stuffing their faces. Besides, what’s the worse that can happen, they tell us to get off their dinosaur?” Dean said.

Dean lassoed the shortest dinosaur, a triceratops, and easily climbed the rope where he straddled the large animal. “I wish I had a cowboy hat!” Dean shouted.

Cas took a half dozen pictures with each of their cameras, thinking that this would be a great story one day. He watched Dean fondly as he climbed down.

“Your turn, Cas!”

“I don’t know how I let you talk me into these things,” Cas complained even as he easily shimmied up the rope. Once on top, he waved to the camera and admired the view from so far up.

“It’s cause I always have such great ideas!” Dean shouted, boasting a bit.

The day was hot, humid, and sticky. They began seeing signs for the Kentucky River Palisades Trail and decided to go. They followed the signs and found a building shaped like an ice cream cone. 

“Come on, I’ll treat you to an ice cream,” Dean offered.

“We haven’t had lunch yet.”

“Well, it’s a little early for lunch and you should never pass up the chance to have ice cream,” Dean declared grandly.

There were two women in the building; one selling ice cream and one selling tickets to the trail. Dean went and got two chocolate cones. Cas was busy talking to the woman selling tickets.

“I’m sorry son, but there aren’t any guided tours for another hour or so. That’s when church lets out,” she explained in a thick Southern accent. “But, two strong boys like you and your friend? You won’t have any problem, sugar.”

“Can we go swimming?” Dean asked, handing Cas an ice cream.

“Well, not right here, but if you go two miles up the road, there’s a swimming hole. Mind you, the water’s a bit cold this time of the year, so you’ll likely have it to yourselves. The water doesn’t really warm up until mid July or thereabouts.”

“Let’s do the trail, Dean. It’s only about two and a half miles,” Cas decided. “We can both use the exercise.

“Okay,” Dean agreed. They paid their fee and were given very explicit directions to the trail. Once they were at the top of the palisades, they were happy they’d decided to come. The Kentucky River meandered slowly down below and the white limestone palisades sparkled in the sun. They were the only people on the trail and the chittering of birds could be heard beneath the cool canopy of the trees.

It took them another hour to finish up the hike and they were hungry. They decided to go into Nicholasville to eat and then double back for the swimming hole. It was only ninety miles to where they intended to spend the night, so there wasn’t much of a hurry to get there.

Rather than waste time in a restaurant, they went into the local grocery and bought ice for their cooler and cold cuts. Sandwiches would do for dinner in the event there wasn’t anywhere to eat in Honeybee.

They found the swimming hole a half mile into a wooded area. Surrounded by massive trees and rocks, it was shaded and cool, and a welcome relief from the humidity of the day. They stilled for a moment listening. No human sounds could be heard nearby. They heard the occasional rumbling of cars in the distance, but it was very obvious they were alone in this stretch of the woods. 

They’d made thick ham and cheese sandwiches before they’d walked in and carried them in along with drinks and towels. They ate a sandwich apiece before the water tempted them. There was a swing rope with a large knot at the end of it. Deciding to take a chance, they stripped down to bare skin before barreling into chill water that took their breath away. They splashed and played until they adjusted to the water, which now felt refreshing.

They raced with no clear winner; they were equally matched. Cas was the stronger swimmer, but Dean had more upper body strength. “If I hadn’t eaten, I would have won,” Cas declared. 

“You keep telling yourself that,” Dean chuckled. “Come here, Cas. I want to kiss you and I don’t know when we’ll ever have the chance to do that in public.”

Cas moved immediately into his arms, reaching for the promised kiss. “Let’s go dry off and finish eating. The sooner we’re behind closed doors the better,” Cas suggested.

~*~

The Cornet ate up the miles to Honeybee. They’d seen the name on the map and Cas had a weird fixation with bees. He thought they were fascinating. Dean was more than willing to indulge his lover’s fixation.

Honeybee was tiny with a Main Street that was a block long. A sign upon entering the hamlet declared a population of 226. Every house and store they passed had a representation of a bee or a hive on it. They were on signs, painted, or sculpted. The Honeybee Hive was a small motel with a diner right next door.

Dean went to check them in. He wasn’t all that surprised to find they were the only guests. Honeybee was a dying town; even Dean and Cas could see that. There was an elementary school, but no high school. Any kids still left in town were forced to go twenty miles to the next town to attend high school.

They unpacked the car and checked out their room. The bedspreads had a bee motif and there were several badly done paintings of bees as well. A card on the dresser listed the types of honey for sale at the check in desk. Cas studied the card intently, mentally cataloging which honey he intended on buying.

“The guy at the check in desk said the diner’s open until 7 PM, but they stop taking orders at 6 PM so we need to get a move on,” Dean informed Cas. “I’ll go shower while you drool over the honey menu,” he grinned.

~*~

It turned out that the owner of the Honeybee Hive also owned and ran the diner. They ordered two orders of honey fried chicken and an order of honey dipped barbeque ribs. The portions were generous and they had enough chicken to take back to the room. The sides of coleslaw, corn on the cob, and green beans were all fresh and delicious.

When Cas inquired about the honey, he was told he could come back in the morning to taste any of them. They allowed customers to sample the honey with homemade honey wheat bread. Cas figured the honey would be a nice gift for Dean’s mother and his brothers.

Their left over chicken wrapped to take with them, they walked back to the room, the humidity of the day slowly dissipating. They could smell the fields filled with fragrant flowers surrounding the small town. Once inside the room, Dean locked the door and pulled the curtains tightly.

“Strip,” Dean ordered Castiel, as he followed his own orders. He steered them into the small shower and they washed quickly. 

Once dry, Dean positioned Castiel on the bed to his satisfaction. “I’m going to trust you not to touch me or yourself, okay? Unless you’d like me to tie you up?”

Dean laughed when Castiel’s already hard cock twitched.

“I’ll keep my hands to myself,” Cas agreed.

Dean’s eyes swept up and down the body of his lover. He liked what he saw. “There’s something I do that I never shared with you,” Dean said as he started to stroke Cas. “Every now and then I’ll have the house to myself and I’ll jerk off.”

“Duh. That’s not exactly news, Dean.”

“True, but what is news is that I won’t let myself come right away. I like to draw it out. I like to bring myself to the very edge and then stop. And then I’ll do that again, and again,” he explained. “I’ve gotten up to an hour, Cas. Just think, an entire hour where I won’t let you come. We’ll work up to that, but for tonight, you can’t come until I let you.”

“Why do you do that?’ Cas asked, panting lightly.

“Because when I finally let myself come, I come so hard I practically pass out.”

“Really?”

“Um hm.” And Dean began his delicious torture of Castiel. He licked broad stripes on the arches of Cas’ feet, sucking on his toes. He licked at nipples, lightly biting until Cas was twisting and pushing his chest into Dean’s face. “Remember, you can move, but you can’t touch me or yourself.”

“I remember.”

“Good,” Dean said spreading Cas’ legs and licking him from hole to balls. He sucked on soft, tightened balls, pressing the heel of his hand against the soft skin of his perineum. He sucked on the fat, swollen head of Castiel’s cock, his tongue circling and licking.

Dean could feel Cas’ cock swell slightly in his mouth and he backed off. He returned to hard nipples, twisting them lightly and blowing on them to harden them even further. Cas was now moaning low and deep.

He returned to the beautiful thick cock, taking it in as far as he could, bringing Cas to the very edge again and then backing off. By now, Cas was practically sobbing and begging to come.

With an evil grin, Dean swallowed Cas down as far as he could, his hand jerking what he couldn’t fit in his mouth. Cas was trying to shove himself all the way down Dean’s throat and he came snarling and cursing.

“You bastard, oh fuck, fuck,” Cas cried, his body arching as he came, before sinking boneless into the bed. 

Dean took him in his arms, gentling him through the aftershocks. He took Cas’ hand and wrapped it around his cock. He was desperate to come. He’d been denying himself as much as he’d been denying Castiel.

He wrapped his hand around Castiel’s and jerked hard and fast. He came within a minute, come splashing across their hands.

“I can’t move,” Cas nudged at Dean. “Go get a washcloth and clean me since you got me messy.”

Dean snorted, but rose from the bed. He swiped the washcloth up and down Cas’ body before tossing it and climbing back into bed. They were asleep within minutes.


	13. Chapter 13

#### Monday, June 29, Day Four

Cas woke before Dean and hopped into a shower, his body feeling loose after yesterday’s hike and the truly spectacular orgasm he’d had. Dean was up by the time he left the shower, smiling and stretching. “Shake those tail feathers. I’m hungry and I want to buy some honey before we leave.”

Groaning, Dean complied. Cas ignored his complaints. It sometimes took Dean a few minutes to fully wake up and he was often grouchy before that happened. A shower helped and he was in his usual good mood by the time they packed the car and checked the room to make sure they didn’t leave anything. They moved the car closer to the diner.

There were a few people eating and they all stopped to stare at the two visitors. Most people they saw were just passing through these days. Not many of them even stopped to buy the local honey any more.

Cas started with the honey tasting and he ended up buying three jars each of five different flavors and a half dozen jars of Tupelo honey. They ate flapjacks, scrambled eggs and bacon for breakfast, with lots of hot, strong coffee to wash it all down.

By the time they’d finished eating, the honey had been neatly boxed for them and they stored the tightly packed boxes in the truck. They said their goodbyes and were on the road driving south towards Tennessee by 7:30 AM. 

“How do you feel about stopping early today?” Dean asked once they were moving.

Cas thought about it for a moment. “Any particular reason why?”

“I figured we could drive to Chattanooga and stay at the Read House. It’s a historic hotel and I thought we could have a look around and then have a good dinner,” Dean explained. “It’d be like a real date,” he blushed.

Cas ducked his head, also blushing. “That sounds really great. How far away is Chattanooga?”

“About a hundred and seventy miles. We could do that in about three hours and have the whole day there.”

“Yeah, let’s do it.”

~*~

Cas walked into The Read House as though he belonged, Dean following and trying to imitate his behavior. He was taken by the Georgian architecture, admiring the majestic line of the building. He was equally taken by the eloquent wood walls that graced the lobby and by the rich leather furniture.

They had no problem getting a room and they made reservations for dinner at 7 PM. They left once they were shown to their room, deciding to go to The Hunter Museum of American Art. The museum’s collection was housed in a classical revival mansion and Cas had to drag Dean inside, while he pled for just a few more minutes to snap photographs.

“Is this the kind of building you want to design?” Cas asked with interest. 

“Parts of it, yeah. The lines are so clean. I want to combine different styles so it speaks of the past, but is modern at the same time,” he enthused.

“If anyone can do that, I have no doubt it will be you,” Cas complimented his lover. “Come on, I heard they have a nice collection of Hudson River School art and I love that style.”

It turned out Dean did as well. They spent two hours walking from room to room and another full hour taking in the Hudson River School art. “I think we found our next vacation destination,” Dean said quietly. “I wouldn’t mind seeing New York City either. What about you?”

“I’d love to go to the Hudson Valley with you. I’ve been to New York once. I didn’t like it at the time, but I was six. I think… I think it might be a good place for us,” he said with a meaningful glance.

~*~

They wandered in and out of some of the shops near the hotel. Cas darted into the drugstore to pick up some postcards as Dean window shopped, still amazed he’d made it out of Lawrence. As much as he’d loved his childhood and growing up there, the town had recently felt like a noose around his neck, dragging him down. Once back in their room, they showered and shaved. Tired, they decided to nap until it was time to dress for dinner, and fell asleep curled into each other. 

They had each brought one suit at Michael’s insistence. Dean was happy he’d made such a stink about it when he walked into the hotel’s restaurant. He’d never been in such a fancy place before. The chairs were padded and upholstered in a deep blue that matched the table clothes. The room was dimly lit, despite the three huge chandeliers. There were candles on every table and more forks, spoons and knives than he’d ever seen at a single place setting.

Once again, he followed Cas’ lead. They both studied the menus. “What are you having, Cas?”

“I’m torn. I don’t know if I want steak or lobster,” he said. Looking up from the menu, he smiled, “No dithering for you, huh?”

Dean laughed. “You know me too well,” he agreed. “I’m going to have the Ribeye, rare, mashed potatoes, and green beans.”

“That actually sounds good. We’ll be eating plenty of seafood once we get to Florida.”

~*~

They shared the elevator with a smiling older couple, who thankfully weren’t in the mood to chat and got off at the seventh floor. They continued their ride to the ninth floor in silence.

“Take your clothes off, Cas,” Dean rasped the second they closed their door.

“Glad to know we’re on the same page as always,” Cas chuckled. 

The moment their suits were on hangers, Cas tackled Dean onto the bed and climbed on top of him, hands reaching for skin. He took Dean’s mouth in a punishing kiss, relishing the sound of his moans.

“I love how you feel on top of me,” Dean admitted.

“Then you’re really going to love this,” he bragged, reaching under the pillow for the tube of KY Jelly he’d bought at the drugstore. 

“And, sometimes you have the best ideas,” Dean allowed, sweeping his hands up and down Cas’ back, enjoying the feel of hard muscle topped by soft, soft skin. 

Cas lubed up their cocks and resettled himself, kissing Dean and thrusting slowly against him. 

They had the luxury of time and privacy. They moved against each other languidly, drawing it out, enjoying every small moment of pleasure. It built and built and they backed off, just kissing and glutting themselves of the feel of each other, of skin against skin, dewed with sweat.

They could feel each other’s thundering hearts, hear the other’s labored breathing, They threaded their hands together as their pleasure intensified, both of them holding back as long as they could.

Castiel’s thrusts became faster and harder, every nerve singing in pleasure. Dean grunted harshly as he came against Cas. Dean’s big hands gripped Castiel’s shapely ass, squeezing gently as he continued to thrust. He came, groaning and writhing against Dean, his pleasure pulsing out. 

They settled themselves to sleep, curled into each other, both of them sated and as content as they’d ever been.


	14. Chapter 14

#### Tuesday, June 30, 1959: Day Five

Dean and Cas showered and checked out, deciding to have breakfast at the cafeteria a few blocks from The Read House. They ate quickly, excited to be alive and on the road. 

“We’re going to hit Florida today,” Dean announced.

‘How far in do you think?”

“Well, we have a couple of choices. Our reservations at the Eden Roc aren’t until Wednesday, so we’re looking at a long drive either today or tomorrow,” Dean said. “I think we should aim for Orlando today and have less of a drive tomorrow.”

“That sounds good. It doesn’t really matter what time we get into Miami; our reservations are set. I’m looking forward to spending mornings in bed with you,” Cas admitted.

“Oh, hell yeah!” Dean agreed. 

“Can we still stop if we see something interesting?”

“Yeah, we could. What time’s check in anyway?”

“2 PM. But, like I said, there isn’t any rush.”

~*~

The scenery in Georgia was much like the other states. Rural landscapes interspersed with small towns. Every now and then a billboard announcing various things would appear, but they didn’t stop until they hit Albany. 

The monotony of the landscape had caused Cas to doze off. He woke once the car stopped moving. “Why are we in front of a giant coffee pot, Dean?” Cas asked, still groggy. 

“Sorry, Cas. I needed to stretch my legs and eat. Also, there’s a mini golf place right up the road,” he grinned. “And the billboard said this place had great burgers and sweet potato fries!”

“That’s different.” Stretching, Cas laughed as his own stomach growled in hunger. Now that he was fully awake, he could smell the delicious aroma wafting out of The Coffee House.

The burgers and fries were as good as advertised. Dean and Cas couldn’t eat them fast enough. Much to the clerk’s amusement, they ordered two additional baskets. “I found the love of my life, Cas. It’s a sweet potato fry!” Dean joked.

The Exotic Putt Putt place featured truly cheesy replicas of famous buildings like the Parthenon and the Eifel Tower. They played two rounds, each of them winning once. They took a lot of photos, mugging for the camera, acting like typical teenaged boys and tourists. 

~*~

It was dark when they reached Orlando. They’d stopped for dinner a few hours ago, taking the fried chicken with them to eat on the road. The billboards for the Wigwam Village had started showing up twenty miles before they hit Orlando, and they weren’t about to pass it up.

There were still two teepees available, much to the delight of Dean and Cas. “We’ve got to get pictures of this tomorrow, Cas.”

They were a little disappointed to find the room was square and had a regular ceiling, so it wasn’t so much like a teepee as it was a regular room in a weirdly shaped building. “Man, what a racket,” Dean noted.

“I bet the little kids like it. We should get pictures of the room for Sam. Otherwise he’ll never forgive us,” Cas said.

Dean grinned, thinking of his baby brother. He was deep into a cowboys and Indian stage and had dragged Dean and Cas to every Western movie showing over the last two years.

“You think he’s ever gonna figure out the Indians don’t ever win?”

“I think he’s already figured it out, Dean. He just _wants_ the Indians to win. Shower?”

“Sounds good. Hand jobs in the shower?”

“Absolutely,” Cas answered his pupils already blown with lust.


	15. Chapter 15

#### Wednesday, July 1, 1959: Day Six

They’d made the decision to only stop at one roadside attraction before they hit Miami. Dean was eager to get to the hotel and see the ocean and Cas was eager to see his reaction to the Atlantic. They’d heard from a number of people at the Wigwam Village that the one not to be missed roadside attraction in Florida was Gatorama in Palmdale. 

Traveling the two lane highway, there was little traffic. They began seeing the signs for Gatorama twenty miles out. The signs, posted every two miles became more gruesome and lurid. The gators got larger along with their teeth. The warnings to keep the faint of heart away had Dean and Castiel laughing hysterically. Five miles before Gatorama, they stopped at one of the many orange groves offering juice and fruit for sale. They bought a five pound bag of oranges and they each chugged down two large glasses of freshly squeezed juice.

When they reached the gator farm they paid the fifty cent fee and proceeded to watch tired looking gators eat chickens. It was interesting to see so many alligators in one place. They dutifully took pictures and visited the gift shop. Dean bought Sammy two gator teeth and as a joke, Cas bought Michael and Gabriel gator jerky.

Laughing, they made their way back to the car, singing ‘See You Later, Alligator’. Windows open, doing 80, they sped along Rte 27 until the end and found Collins Ave. Miami Beach was like no other town they’d ever seen. It was tropical, filled with palm trees and the constant roar of the ocean could be heard beneath all the noise that typified Collins Ave.

Castiel pulled in front of the Eden Roc and left the car running. By the time he and Dean grabbed their suitcases, there was a bellhop and a valet waiting to park the car and take their luggage. They were escorted to the front desk in the grand lobby. 

Dean looked around, impressed despite himself. It was a huge gleaming space, filled with columns, and a sparkling chandelier, and ample seating space for those that wanted to relax. He’d never been in so grand a place and he decided on the spot this was something he wanted to get used to. His mind was busy cataloging the architecture, and the use of space.

The young uniformed man seemed confident until Castiel mentioned their names. “One moment, sir. Please let me get the manager.”

Moments later, a well dressed older man appeared. “Mr. Novak, Mr. Winchester. We have a small problem,” he began.

Sighing, Cas asked, “What kind of problem?”

“The room reserved for you was flooded last night and I’m afraid we don’t have anything similar. Of course, we plan on giving you a room, but you and Mr. Winchester will be required to change rooms in a week,” he explained.

“Well, that’s inconvenient,” Cas said snottily. 

Dean held in his snort of laughter. Over the years he’d seen how the Novaks lived and it was a different world from the one he knew. It was amusing to see his lover change into the rich kid right before his eyes.

“I agree, Mr. Novak. Your family’s business has been appreciated from the time we opened our doors. Both rooms will of course be upgraded and all your meals at the hotel will be complementary,” the manager offered.

“For the entire two weeks?”

“Yes, of course. That would also include room service. Your brother Michael was quite clear about the fact he wanted you and your friend to enjoy yourselves.”

Cas turned to Dean. “What do you think?”

“It’s not like we have much of a choice.”

“True,” Cas agreed. “Fine, if we could be shown to our room now. You’ll make sure the kitchen knows we aren’t to be charged for room service?”

“Of course, Mr. Novak.”

Dean tipped the bellboy and whistled when he saw the room. Two Queen size beds, a generous seating area, a large bathroom and a balcony big enough to fit both their families, and all decorated in the latest style. “Wow, Cas! This is amazing. And free food,” he crowed, picking up the room service menu.

“What do you want to do first,” Cas grinned.

“Eat. And since you’re not supposed to swim for an hour after eating, maybe we can put one of the beds to use,” Dean suggested, eying Cas with heat.

“Sounds like a plan. Go shower. I’ll order. Turkey club and fries?”

“Yeah. Perfect.”

The food arrived just as Castiel was getting out of the shower. Dean had rolled the food cart out to the balcony. The sound and scent of the ocean was spiking his hunger and the sight of Cas wrapped in one of the thick towels sparked a wholly different appetite. He watched with amusement as Cas slipped on a pair of shorts.

“We could probably sit out here naked and no one would see,” Dean teased.

“I notice you aren’t naked,” Cas observed.

“I didn’t want to scare the guy bringing up the food.” Dean remarked.

“Point,” Cas acknowledged as he sat down. “Wow, it’s gorgeous. I can’t wait to hit the ocean.”

“Yeah, it certainly is gorgeous,” Dean agreed, his eyes on Castiel.

“Dean,” Cas groused.

“What? I’m a healthy eighteen year old guy.”

They ate, savoring the meal, both of them feeling the sexual tension rise.

When they were finished, they wheeled the cart back in and closed the drapes, creating a private oasis. Castiel stripped off his shorts and reached for Dean’s shorts, unbuttoning them and sliding them down. He was pleased to see his lover had foregone underwear.

Castiel sank to his knees and took Dean’s already hard cock into his mouth as far as he could. The slight press of hands on his head turned him on and his desire spiraled. “Go sit on the bed,” he instructed, pulling off Dean.

Kneeling once again, his head bobbed up and down between Dean’s spread legs. He slid his hand under Dean and his calloused thumb stroked the slightly swollen perineum, forcing groans from his lover.

“Fuck, Cas, you are getting so good at this. I wanna come in your mouth.”

Eyes signaling yes, Castiel continued blowing Dean until he spilled into his mouth. Shuddering through his orgasm, Dean pulled his lover onto the bed once the aftershocks stopped wracking his body, kissing him deeply.

“Your turn. I think I’m gonna have to get a lot more practice in before I get as good as you, though,” Dean said between sucking kisses on his way down.

Cas moaned, “Practice is good. Very good.”

~*~

Dean and Castiel spent their two weeks in Miami eating good meals, making love, swimming for hours in the ocean and sunning themselves by the pool. They walked the beach finding and collecting seashells to bring home. They took in the local sights and made sure to stuff themselves a few times a week at Joe’s Stone Crab shack. 

And they fell in love, deeper and deeper every day. They didn’t talk about it; neither felt ready. It was too new and too special. But, their love wasn’t fragile. It was anything but. Dean and Castiel had known each other for years. They had a shared history and knew the other’s faults and strengths. They complimented each other to an untold degree. Where one had a weakness, the other had the strength to make up for it. So, they just enjoyed it. The time to talk would come; it had to. There were things that needed to be discussed, but it would wait.

The night before they left, they stood by the ocean on an empty beach. The pounding surf mesmerized Dean. He looked at Castiel and smiled. “This is amazing. It’s so big and powerful. It makes me feel, I don’t know. Small maybe?”

“In the scheme of things we’re all small. The trick is to live as big as you can.”

“No, Cas. I think the trick is to have as much love as you can. I don’t care if we don’t have big lives.”

“When did Dean Winchester get so philosophical?” Castiel laughed.

In answer, Dean began to sing;

“Never felt like this until I kissed ya  
How did I exist until I kissed ya  
Never had you on my mind  
Now you're there all the time  
Never knew what I missed til I kissed ya, uh-huh  
I kissed ya, oh yeah

Things have really changed since I kissed ya, uh-huh  
My life's not the same now that I kissed ya, oh yeah  
Mmm, ya got a way about ya  
Now I can't live without ya  
Never knew what I missed til I kissed ya, uh-huh  
I kissed ya, oh yeah

You don't realize what you do to me  
And I didn't realize what a kiss could be…”

~*~

They’d decided at the last moment to continue on to Key West. It seemed stupid to be so close to the very end of the United States and not take the opportunity to see it. The directions seemed simple enough, take the Knights Key-Pigeon Key Bridge, otherwise known as the Seven Mile Bridge to the end.

They were nearing the end of the bridge and Key West when they say the elderly woman flagging them down on the other side of the road. It was apparent she had a flat and was looking for some help. She started chattering the moment Dean pulled over.

“Oh, boys, I’m so glad to see you. I’ve been here for an hour and my son won’t miss me for at least another two hours, and it’s so warm,” she said fanning herself.

No wonder Dean thought, she was dressed in a sweater set. “You have a spare tire, Ma’am?” 

“I don’t know what all Gary has,” she declared. “He and Peter will be so angry that I didn’t wait for them to take me to see my sister. I keep telling them I may be old, but I’m far from feeble,” she ran on, patting her iron gray bun in place.

Dean popped the trunk and found the spare. He and Cas had the tire changed within fifteen minutes.

“Thank you, boys. I insist you come back with me. Gary won’t go on and on if you’re with me. And I’m sure he’ll want to thank you personally. I’d like to put you up for a couple of days. We’ve got a pool and we have the best cook in town,” she chattered.

Castiel looked at Dean and shrugged his shoulders. They hadn’t been planning to stay, but it would be hard to say no to Gertrude Williams and her overwhelming personality. It was quickly decided that Dean would drive Mrs. Williams’ car and Cas would drive the Coronet.

Mrs. Williams directed Dean to a large piece of property a block from Duval Street. There was a large wrap around porch with a discreet sign reading Land’s End. The house was sizable and Ms. Williams shooed them into it. From there they could see what appeared to be a dozen or so small bungalows surrounding a large in ground pool. Two men in their mid forties slammed out of the interior of the house when they heard the front door opening. Both men ran to greet Mrs. Williams. “Mom, why didn’t you wait for us?” the shorter man demanded.

“Mom, one day you’re going to get into trouble that you won’t get out of,” the taller man scolded.

“Pshaw.” Tugging on the arm of the shorter man, Gertrude turned to Dean and Cas. “Boys, this is my son Gary, and that is his gentleman friend, Peter.”

“Gary, Peter, these two young men changed my flat tire. I want for them to stay with us for a few days. As a thank you. I’d still be stuck on the road if not for them,” she drawled, her Southern accent becoming more pronounced. 

Dean saw Gary and Peter exchange a look. Gary escorted his mother deeper into the house and Peter approached the two boys. “Look boys, you’re more than welcome to stay for a few days,” he started, shifting from one foot to the other. “You should know that this is a gentleman’s only resort. I don’t want you or any of our guests to be uncomfortable.”

Cas’s eyes slid to Dean’s face where he read confusion. “We understand, Peter,” Cas replied. “This is a resort for…”

“Gay men,” Peter supplied.

“I… We won’t be uncomfortable,” Cas stated. “We’re…” he began and stopped awkwardly. 

Peter studied both boys carefully for a moment. “I see. It will be our pleasure to have you as our guests. And, thank you for helping Gertrude. She’s headstrong and she forgets she’s getting on a bit,” he said. “Come with me and I’ll get you settled.”

Peter led them to one of the small bungalows surrounding the pool. It consisted of a small tastefully decorated sitting area, a sizable bedroom in muted, masculine colors with a King size bed piled high with pillows. The bathroom in shades of ocean green and blue contained a decadently sized bathtub and lots of plush towels. “For some of our guests, this is the one place they may have where they can be comfortable and be themselves for a couple of weeks a year. We try and make it as inviting as possible. The kitchen is opened from 6 AM to 5PM. Most of our guests eat lunch poolside and go out for dinner. We set up a breakfast buffet poolside, which closes at 9.”

“Thank you, Peter. We appreciate your hospitality,” Castiel said.

“You’re welcome. And if you leave Land’s End, be careful. In fact, you should get used to being careful. For your own safety,” Peter urged.

“We will be,” Dean promised.

~*~

They spent part of the next three days wandering around Key West, shopping on Duval Street and watching the sunset from Mallory Square. They drank lots of Cuban coffee and ate Key Lime pie everyday along with other local specialties. They took the time to sit for one of the many artists to have their portrait done. They picked up small souvenirs for their families at the Old Island Trading Post, laughing at the tacky items, but buying whatever caught their eyes anyway, and generally had a lot of fun just goofing around. Their cameras were always out and in use.

Most of their time was spent at Land’s End. The pool was large enough that it never seemed overcrowded and the other guests were friendly but not nosey. Music was always playing and Dean and Cas soon got used to seeing men dancing together. They were comfortable enough to join in and it was freeing. And sexy. The ability to publically claim each other and to kiss or hold each other in front of others was normal and expected here. They knew it would not be like that outside the gates of Land’s End and they took full advantage.

They made a point of taking long baths together not knowing when they’d get the chance again. Cas had already told him the bathtub in the Iowa apartment was standard size. The best part of each day was when they retired to the big comfortable bed. 

It was on their second night that Dean decided to ask for something they hadn’t yet tried. “I want you to fuck me, Cas.”

“I thought we weren’t ready for that yet.”

“I am now. I want to at least try,” he said, tossing the small tube of KY Jelly on the bed.

Cas kissed Dean tenderly, undressing him slowly. He sucked at his cock, stroking the cleft of his ass. “Turn over, Dean. I want to taste you.”

Dean immediately complied, shoving a plump pillow beneath his hips as he turned on his belly. Cas stared at the pert, smooth ass, stroking gently. Dean was in good shape and his ass was tight and muscular. Spreading his lover’s legs, Cas knelt and spread the globes of Dean’s ass. He bent and took a long loving taste, running a soft tongue up and down. 

A groaning and squirming Dean had Castiel redoubling his efforts. He bit lightly at Dean’s pucker, feeling his lover relax beneath his mouth.

“Now, Cas, start putting your fingers in me, one at a time,” Dean demanded.

Using plenty of lube, Cas complied, twisting his fingers, searching for the small nub he’d read about. He knew he’d found it when Dean gave a long shudder, his breath coming in short sobs. “Now, Cas, please. Get inside of me,” he begged.

Castiel lined himself up and pushed in slowly and carefully. When he was fully seated, he panted, “Just let me know when you’re ready.”

“Cas, this is so amazing,” he said in wonderment. They rested for a few minutes, allowing Dean to get used to the feeling of being filled. 

“Now, Cas.”

Cas began with short, slow thrusts, angling himself to nudge against Dean’s prostate. On his fifth thrust, Dean gasped and began pushing back. “Fuck, that’s so good.”

“Yeah, it sure is. You’re so tight, Dean. This feels so fucking good.”

“Harder, Cas.” Dean groaned clutching at the sheets and sweating freely.

Cas bent his knees a bit for more leverage, shaking the sweat out of his eyes and gave Dean just what he wanted. He felt Dean stiffen beneath him, felt his ass spasm around his cock, and heard Dean come cursing and groaning. He came shortly after in exquisite ecstasy that skidded the edge of pain in its intensity. 

He managed to collapse to the side of Dean, his breath labored and heart pounding. He stroked Dean’s arms and slid out of him carefully.

Dean turned to him, and kissed him. “That was even better than I thought it would be. I didn’t think it was possible to come that hard,” he whispered.

They washed and collapsed into bed, deeply asleep within minutes. 

~*~

They danced until past midnight on their last night in Key West. Tomorrow they would be heading back to Kansas and their future. They lay in bed, Cas being held tightly by Dean. The room was softly lit and they could hear occasional shouts coming from the pool. “Do you really think we can make this work?” Castiel asked, his voice soft and worried.

“Yeah, Cas, I do. We’ll have to be damn careful, especially at school, but I won’t give you up. Not now, not ever,” Dean confessed. “I’m in love with you. I think I’ve been falling in love with you for a really long time.”

“I’m in love with you too, Dean. I’ll… I’ll do whatever it takes to be with you,” he admitted. “How do you think your parents are going to react?”

Dean chuckled. My mother said something to me the day we left. I - - I didn’t get it at the time. But I get it now.”

“What’d she say?”

“She told me that when I find something I love, I should grab onto it with both hands and never let go. She said it didn’t matter what anyone else had to say about it,” Dean recalled. “I think she figured out we were in love a long time ago, Castiel.”

“What about your dad?”

Laughing again, Dean said, “You must have noticed by now he’s a little hen pecked. He’ll go along with whatever my mother tells him to go along with. Anyway, he won’t be supporting me.”

“I think Michael goes out of town to sleep with men,” Castiel disclosed. “I’ve seen him with women in Lawrence, but nothing that’s ever lasted more than a few months.”

“And Gabe?”

“Gabriel loves me. He just wants me to be happy. He also talks to your mother on a regular basis. It wouldn’t surprise me at all if they’ve already discussed this.”

“We’ll be okay, Cas. We’ll be careful and who’s to say what goes on behind closed doors? We’ve been best friends our whole lives. We’ll do whatever we have to in order to stay together and safe,” Dean decided.

“We’re going to have a great life, Dean.”

“Yeah, babe, we are,” Dean agreed, tightening his arms around Castiel and silently vowing to never let him go.

### Epilogue

#### Washington, DC, June 26th, 2015

The aspiring journalist got lucky. In the years to come, he’d use the words supremely lucky. It was his idea of a little pun or a joke as the photos seen around the world were shot in front of the Supreme Court. Not wanting to wade into the cheering, rejoicing throng, he was walking around the perimeter of the crowd, snapping random photos with his cheap digital camera.

He caught the elderly, dapper men in three different frames. One, as they looked into each other’s eyes, smiling softly, the next as they began to kiss, and the last as they continued to kiss while the taller of the two lifted up the smaller man and swung him around.

Larry approached the two men and began asking his questions. When he discovered that they’d been together since 1959 and had just celebrated their 11th wedding anniversary, he knew he’d hit pay dirt. He asked a few more questions, stomach clenching with excitement.

He found a quiet spot away from the jubilant celebrating crowd and quickly wrote up the article. He began shopping the photos and interview around an hour later.

Every major media outlet on the planet wanted to buy what he was selling. And the photos that graced every major newspaper, both print and digital the next day showcased one or more of the photos of Dean and Castiel Novak Winchester, their love for each other on display for the world along with their decades long love story.

After all, who but the coldest cynic doesn’t love a love story?

~*~

“What was it like when we fell in love?” Dean repeated the question, his still vibrant bottle green eyes softening. “Sometimes your whole world changes between one blink of your eyes and the next,” Dean reminisced. “It was like suddenly being able to see the world in sharp focus. That’s what it was like when we fell in love.”

Dean Novak Winchester

“Being gay back then was… isolating in some ways. But, Dean and I were committed to being together no matter what it took. We were lucky, though. Both our families were supportive and didn’t care as long as we were happy. We had good friends and they never cared either. And then we were able to marry,” Castiel said, deep voice softened. “And now look,” he exclaimed. “I can kiss my husband in public and no one cares.”

Castiel Novak Winchester

“When did I know for sure?" Dean laughed. “I think I always knew on some level that I loved Castiel. But, it wasn’t till I kissed him that I knew for sure. After that I knew I was never going to give him up. And we’ve been together from that day.”

Dean Novak Winchester

_Excerpts from Newsweek Magazine_

 

 

The End

**Notes for the Chapter:**

> I thank everyone who has read this and left comments and kudos. It was awesome engaging with readers.
> 
> I think there are many stories still be told here and if there is anything you'd like to read about, leave me a prompt.

**Author's Note:**

> Dean and Cas start school in 1st grade. Kindergarten was not mandatory at the time. 
> 
> This was insanely hard to research. Rather than go for complete accuracy, I decided to incorporate elements from many different places into Dean and Castiel’s road trip. I’ve also changed the date of the State Fair. (The State Fair they stop at always takes place in August and not in June, although Gene Autry did in fact perform at the fair in 1959.) If there are any inconsistencies with what you know, call it poetic license.
> 
> So, if I’ve used a roadside attraction that didn’t really exist in 1959, or from your state, but placed it in a different state, my apologies in advance, and I already know. It was not done out of ignorance, but in order to give Dean and Cas a place to stop and have fun or marvel over the silliness that many of the old roadside attractions offer us today, and certainly back in the ‘50’s. I only chose to use a few of them, but I encourage you to search them out in your state, even if they’ve been abandoned. They speak to us of a different time and are fast disappearing.
> 
> The road trip and the accompanying roadside attractions are a uniquely American thing and decades later, even the ruins of such places call to us. They wind their brash Americana and unique personalities around us, evoking a nostalgia that few of us are able to resist. Of course, life in the ‘50’s sucked for many; minorities, in particular African Americans, women, and those in the LGBT community. That’s the part that gets left out for those who continue to tell us the ‘50’s were the best time for this country. And, if you were white, straight, and male, that’s true.
> 
> ~*~
> 
> The highway system that we know today did not exist in 1959. I found a really helpful person at the Federal Highway Administration, who was not only willing to talk to me, but also provided me with several maps from the time period. Thanks, Richard. If I’ve gotten anything wrong, it’s my fault.
> 
> Thanks to the Lawrence Historical Society who gave me a feel for what Lawrence was like in the late ‘50’s. They were very helpful and I enjoyed speaking with them tremendously.
> 
> Thank you to the Kentucky Bureau of Tourism. I spoke with a very knowledgeable person who patiently answered my questions and was kind enough not to mention my East Coast accent.
> 
> In trying to get a feel for the area in the late ‘50’s, I spoke with an African American woman in Chattanooga, Tennessee, who grew up under segregation. She told me a number of stories about what life was like for her in the ‘50’s and the impact segregation had on her. She was kind enough to spend a great deal of time with me, and when I hung up, I cried. She was lovely and I’m sorry she had such terrible experiences. 
> 
> I’d also like to thank the older gay men who were very open about their experiences growing up and willing to share with me. It is inconceivable to me to grow up and to discover you’re different and made to feel fear and shame instead of pride and acceptance. Things are getting better, but there is still work to be done.


End file.
